


Looks Can Be Deceiving

by NavajoLovesDestiel



Series: NaNoWriMo one shots [11]
Category: Supernatural
Genre: Alternate Universe, Anal Sex, Bottom Castiel, Cas is a crossdresser, Castiel in Panties, Crossdressing, M/M, Smut, Top Dean
Language: English
Status: Completed
Published: 2017-11-10
Updated: 2017-11-10
Packaged: 2019-01-31 12:45:39
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,525
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12682173
Author URL: https://archiveofourown.org/users/NavajoLovesDestiel/pseuds/NavajoLovesDestiel
Summary: Dean walked in, sat at the bar and ordered his usual beer. He’d had a bad day at work and just came in to relax. His eyes scanned the room casually, until he saw her. She was sitting alone in a booth. She was stunning.





	Looks Can Be Deceiving

**Author's Note:**

> Written for NaNoWriMo

Dean walked in, sat at the bar and ordered his usual beer. He’d had a bad day at work and just came in to relax. His eyes scanned the room casually, until he saw her. She was sitting alone in a booth. She was stunning. Messy short dark hair, makeup perfect. From what Dean could see, she really had a rocking body. He sipped his beer and kept an eye on her, hoping she wasn’t here with anyone.

Time passed and he finished his beer and got another. He stood up and casually walked towards her booth. Maybe his day was about to get better.

“Can I buy you a drink?”

She looked Dean up and down, then nodded. Dean turned and got the bartender’s attention, signaling for 2 more drinks.

He sat down. “My name is Dean Winchester.”

She smiled. “Cassie Novak.” Her voice was low and husky and sexy as hell.  Dean wanted her to talk a lot more.

“So alone tonight?”

Cassie smiled. “Yes, I am. Just felt like getting a drink.’

Dean smiled at her. “Well, that was lucky for me.”

Their drinks arrived. Cassie smiled and took a sip. “Thank you for the drink, Dean.”

Dean smiled. “It’s nothing.”

Cassie asked what Dean did for a living. He told her about how his adopted father had retired and left him a garage.

“So, you fix cars? I love a man who works with his hands.”

Dean took that for flirting. “Oh, I have very talented hands.”

“Oh do you, Mr. Winchester?” Cassie smiled at him through her lashes.

Dean grinned and took a long draw on his beer.

A song came on the jukebox and that led them to discuss music. The conversation went on to movies and television shows.

A couple of drinks later, Dean thought it was time to put the moves on this lucious piece of womanhood.

“Cassie, can I give you a ride home?”

Cassie smiled. “Well, that depends…”

Cassie slid over next to Dean. She took his hand and put it directly on her crotch.

Dean felt a cock. He fingered it and it was definitely a cock.

His eyes got big.

“Well? Can I give you a ride home or not?”

Cassie grinned. “It depends on whether or not you want to fuck me or beat me up.”

Dean frowned. “I want to fuck you. And men have beat you up?”

Cassie sighed. “More often than I care to admit.”

“That’s fucked up. I’m sorry. And I would never hit a lady.”

Cassie smiled sadly. “Even if the lady is a man?”

“Even then. I happen to like men.”

“Then what are you waiting for? You offered me a ride.”

Dean stood up. He turned to Cassie, “Uh, you aren;t a hooker are you?”

Cassie grinned. “No, Dean, I’m not a hooker.”

Dean blushed. “Okay I was just checking. I don’t usually get this lucky.”

Cassie had runner’s legs. Her thighs were just the right amount of thick, Dean took a good long look at them and her beautiful ass as she walked out in her very short skirt in front of him.

Dean guided her to his car, opened the door for her and then got in. Cassie gave him directions.

When they got to Cassie’s apartment and got inside. Cassie turned to Dean.

“Get comfortable. I have to pee. I never pee in public and I think you can guess why.”

Dean could definitely guess why. He sat on the couch and waited. Soon, Cassie came back,

“That’s relief. Now…” Cassie pulled Dean to his feet and grabbed his shirt, pulling him to her.

She kissed him and he pulled her closer.

They kissed for a while. Dean’s pants were getting tight, and he definitely felt Cassie was getting excited too.

Dean pulled away. “So, Cassie, are you transgendered or what?””

Cassie smiled. “No, I just like dressing up in women's clothes. Just your average, every day crosssresser.”

“Nice..” Dean smiled. 

Cassie grabbed his hand and led him to the bedroom. Dean grabbed her and kissed her again. 

“What’s your real name?’

‘You do ask a lot of questions, Dean. My name is Cas. Short for Castiel.”

“Cas… Cassie… cute.” Dean kissed him again. He was now a man in Dean’s mind, especially with his cock prodding Dean’s thigh.

“Too many clothes, Dean.”

Dean grinned and stepped back. He began to strip. When he finally pulled down his boxers and his cock sprang free, Cas whistled.

“You’re really packing there, Dean.”

Dean just laid down on the bed. “Your turn, Cas.”

Cas began to take off his clothes. He first pulled his blouse over his head, revealing a padded bra. Then he unzipped his skirt and stepped out of it. He was wearing lacy panties, and his cock was hard and peeking out of the top.

Dean licked his lips. He laid and watched Cas unhook his bra and take it off,

“Leave on the panties, Cas, please.”

Cas grinned and laid down next to Dean.

Dean pulled Cas closer and kissed him, hot and messy. He ran his tongue along Cas’ lips and Cas opened his mouth for it. Dean ran his tongue over Cas’ and it was so hot he explored the rest of Cas’ mouth..

Dean broke the kiss and began to kiss along Cas’ jaw and behind his ear. Cas shivered.

Dean worked his mouth down Cas’ throat and to one nipple. He sucked it to hardness and then did the other one.

Cas moaned. Dean really liked the sound.

Dean licked and kissed his way to the top of Cas’ panties. He licked over the head of Cas’ cock and Cas groaned.

Dean put his mouth on Cas’ cock, sucking and licking it through the soft material. Cas was making the most wonderful sounds and Dean kept it up. 

Cas spread his legs and Dean licked Cas’ balls, tucked up in the panties. 

He manhandled Cas onto his stomach and spread his legs wide.

He shoved his face in between Cas’ thighs and nuzzled his balls. Cas moaned and thrust his hips up.

Dean moved up and pulled down Cas’ panties from his amazing ass. 

“Lube, Cas?”

Cas grabbed the lube from the bedside table and handed it back to Dean. Dean grabbed it and lubed up his fingers,

He ran one finger around Cas’ hole and Cas made the most delightful sound. 

Dean shoved his finger into Cas and Cas tightened on it, then relaxed. Dean pushed his finger in all the way and began to move it in and out of Cas. He added a finger and Cas pushed back on them. Dean let Cas fuck himself on his fingers. It was so hot.

Dean added another finger and worked Cas open. Finally, He asked Cas for a condom. Again, Cas reached and grabbed one from the bedside table and handed it back,

Dean rolled it on and lubed it up. Then he pulled back on Cas’ hips to lift his ass in the air. 

Dean pushed into Cas and Cas sighed. 

“Fuck! You feel so good, Dean.”

Dean smiled.”You ain’t felt nothin yet, baby.”

Dean pushed in all the way, and paused to let Cas adjust.

Cas groaned. “Move, Dean, now!”

Dean chuckled, “Okay, bossy.”

Dean began the pull and push, just loving how Cas felt. He leaned over and kissed Cas on his spine.

Cas demanded he go faster and harder, so he increased his speed and began to snap his hips against Cas’ ass. All that could be heard was moans, groans and the sound of skin slapping against skin.

Finally, Dean could feel how close he was, so he reached around with the hand that had all the lube on it and grabbed Cas’ cock. 

“Fuck! Dean!”

“Cum for me baby. I’m so close…”

It only took a few passed up and down Cas’ cock and he was coming. He cried out and clenched down on Dean’s cock. That was all it took for Dean to cum as well.

Dean groaned out Cas’ name. He put his head in between Cas’ shoulder blades and tried to catch his breath.

When he could breath, he pulled out and pulled off the condom. He tied it off and tossed it in the trash. Then he laid down next to Cas, and pulled him close.

He kissed Cas’ sweaty forehead.

“That was…”

Cas grinned. “Amazing? Fantastic?”

“Both of those and more, Cas.”

They lay cuddled together. 

Dean lifted his head and looked at Cas.

“I think I need to take you out on a date, What are you doing tomorrow night?”

Cas smiled. “Nothing. Same as every night.”

“Well, I’m going to change that, baby. Every night is gonna be full from now on.”

Cas smiled as Dean kissed him.

They were a couple from then on. When Cas came for the first time to Dean’s work, he was wearing a sundress.

“This is my boyfriend, Cas.”

No one said a word.

When they got married, Cas wore a wedding dress. 

Everyone said he was the most beautiful groom they’d ever seen.   
  



End file.
